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544051

Sigma-Aldrich

L-Homophenylalanine hydrochloride

97%

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About This Item

Linear Formula:
C6H5CH2CH2CH(NH2)CO2H · HCl
CAS Number:
21176-60-3
Molecular Weight:
215.68
MDL number:
MFCD03427064
UNSPSC Code:
12352209
PubChem Substance ID:
24878289
NACRES:
NA.22

Assay

97%

optical activity

[α]20/D +38°, c = 1 in 3 M HCl

reaction suitability

reaction type: solution phase peptide synthesis

mp

262-265 °C (dec.) (lit.)

application(s)

peptide synthesis

SMILES string

Cl.N[C@@H](CCc1ccccc1)C(O)=O

InChI

1S/C10H13NO2.ClH/c11-9(10(12)13)7-6-8-4-2-1-3-5-8;/h1-5,9H,6-7,11H2,(H,12,13);1H/t9-;/m0./s1

InChI key

CHBMONIBOQCTCF-FVGYRXGTSA-N

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Sonja Nordhoff et al.
Bioorganic & medicinal chemistry letters, 19(16), 4818-4823 (2009-07-07)
A series of highly potent and selective inhibitors of DPP-4 was optimized for ADMET properties. The effort resulted in the discovery of inhibitor 1g, that exhibits excellent efficacy in an oral glucose tolerance test and an attractive pharmacokinetic profile.
Kento Koketsu et al.
Applied and environmental microbiology, 79(7), 2201-2208 (2013-01-29)
L-Homophenylalanine (L-Hph) is a useful chiral building block for synthesis of several drugs, including angiotensin-converting enzyme inhibitors and the novel proteasome inhibitor carfilzomib. While the chemoenzymatic route of synthesis is fully developed, we investigated microbial production of L-Hph to explore
Patrycja Drygała et al.
European journal of medicinal chemistry, 44(9), 3731-3738 (2009-06-03)
Immune response suppressors are used in the medical praxis to prevent graft rejection after organ transplantation and in the therapy of some autoimmune diseases. Cyclolinopeptide A, naturally existing immunomodulatory peptide, was modified with homophenylalanine in positions 3 (4), 4 (5)
Tasir S Haque et al.
Peptides, 31(5), 950-955 (2010-02-09)
We report the identification of potent agonists of the Glucagon-Like Peptide-1 Receptor (GLP-1R). These compounds are short, 11 amino acid peptides containing several unnatural amino acids, including (in particular) analogs of homohomophenylalanine (hhPhe) at the C-terminal position. Typically the functional
Sonja Nordhoff et al.
Bioorganic & medicinal chemistry letters, 19(22), 6340-6345 (2009-10-17)
For a series of beta-homophenylalanine based inhibitors of dipeptidyl peptidase IV ADME properties were improved by the incorporation of amide replacements. These efforts led to a novel series of potent and selective inhibitors of DPP-4 that exhibit an attractive pharmacokinetic
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